How do you redesign a life at 50 - agile and without regret?

In this episode, Robert talks with technologist and agile coach Reggie Valentine, whose career spans reinsurance, dot-com media, and fintech. Reggie shares how discovering Agile changed not just his projects but his approach to life: prioritize, time-box, learn fast, and pivot without remorse.

Robert and Reggie discuss 70-hour workweeks, a year “retired” in Belize, and why being “The Wolf” who fixes a mess beats chasing prestigious titles. Reggie reflects on AI as a time dividend, the wisdom of finishing over starting, and why experiences matter more than things.

This one’s about dropping old backlogs, re-prioritizing your life, and keeping curiosity alive in midlife.

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